Ammonium formate → Ammonia

HRID 1433248Notes

Reaction equation

[C:1]([O:5][C:6](=[O:51])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18]/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][C:24]([O:27]CC3C=CC=CC=3)=[C:23]([C@@H:35]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:36][CH2:37][N:38]([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[CH:22]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:7].[C:1]([O:5][C:6](=[O:51])[NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C@@H:35]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:36][CH2:37][N:38]([CH:42]([CH3:43])[CH3:44])[CH:39]([CH3:40])[CH3:41])[CH:22]=2)=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-butyl[2-(4-{[(3E)-4-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}but-3-en-1-yl]oxy}phenyl)ethyl]carbamate (Preparation 11, 725 mg, 1.05 mmol) was dissolved in ethanol (10 ml), palladium hydroxide (20% by weight on carbon, 181 mg, 0.25 mmol) then ammonium formate (529 mg, 8.39 mmol) was added and heated to 80° C. for 5 minutes then stirred at 75° C. for 1 hour. Reaction was cooled to room temperature and the mixture was filtered through Arbocel™ and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97/3/0.3 to 94/6/0.6 by volume) to yield the title compound as a white foam, 460 mg.

Workup

customReaction
temperaturewas cooled to room temperature
filtrationthe mixture was filtered through Arbocel™
customthe solvent removed in vacuo
customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record: ord-76ead1cd03624e14b5d6b1c5850ee27f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612084B2

Reaction notes

Loading…